Just Getting Started

Finish the Prologue
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Survivor
Survive first encounter with the Crooked Man

During Scene 1, after your first encounter with the Crooked Man.
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Scene 1 Complete!

Finish Scene 1
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Scene 2 Complete!

Finish Scene 2
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Scene 3 Complete!

Finish Scene 3
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Scene 4 Complete!

Finish Scene 4
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Bye-Bye Black Bird

Beat the Game - the achievement will spawn after the credits.

What a Sissy

Get Bad Ending 1 - meaning after your battle with the Crooked Man, choose the wrong dialogue option with Sissi. Please, don't cry... Scene 1.
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Never, Ever Give Up

Get Bad Ending 2 - meaning choose the wrong dialogue option with D towards the end when given the choice. You shouldn't give up. Scene 2.
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Goodbye, My Friend!

Get Bad Ending 3 - meaning choose the wrong option when David is in a very perilous situation. [You are controlling Paul at this time.] Choose to Persuade David. Scene 4.
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Not Your Fault, David!

Get Bad Ending 4 - meaning choose the wrong option when David is in a very perilous situation. [You are controlling Paul at this time.] Choose to Take the Gun. Scene 4.

Just Let Me Sleep!
Go back to bed without answering the phone

Obtainable in the Prologue. When David wants to go to sleep, but is interrupted by the telephone, just go to bed.
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Screams of the Sightless
Read the books in the hotel library

Scene 1, at the hotel. There is a single book in the library - be sure to read it.
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Game Over
Get Game Over once

I highly doubt anyone can play through this and not get this achievement, but it is technically missable. Just get killed by the Crooked Man; I don't think Bad Ends count.
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COME TO ME
Get Game Over 5 times

Get Game Over 5 times. Again, I doubt anyone wouldn't get this naturally. But technically missable.
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Uncrooked Man
Defeat the Crooked Man in Scene 1 without taking any damage

Defeat the Crooked Man in Scene 1 without taking any damage. This is one of the few achievements testing your battle skills. Remember to depend on the range of your knife. I find it very helpful to stick to a strategy of swipe at him, then run, swipe, then run. Get a rhythm going and it shouldn't be that hard.
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Self-Loathing
Read the books in the school

There is a book singled out on the table in the Reference Room of the school in Scene 2. Read this book for the achievement.
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Precious Drink

During Scene 2, D gives you an energy drink. Do not drink it. Keep it with you to the end of the game and you should get this achievement automatically. Possibly a subtle BL joke (as also referenced later), in the drink D gave him being so precious? Hmm...
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Gas Chamber
Get killed by poison gas

When you and D are trying to get out of the basement that is leaking gas, let the time run out (or just fail to figure out how to get out). Another achievement I can see many players just get naturally.
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Speed Runner
Escape the gas with over 1 minute to spare

Escape the gas with over 1 minute to spare. Meaning, not referring to the game itself. Again, for a section in Scene 2 when you and D need to escape the basement. Once you figure out how to get out, or otherwise look it up, be quick with your movements and it's fair to expect to be able to be 5-10 seconds over a minute. Just do what you need to, once you're not clicking everything trying to figure out what to do.
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BL?!
Try to enter D's bed

Short for "Boys' Love", otherwise known as Yaoi or (male) gay romance. A joke achievement for Scene 2, after the "gas chamber" portion. When D is in bed, recovering in the infirmary, move to get in bed with him.
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Sick Leave
Try to enter the bed next to D's bed

Also after the "gas chamber" segment. When D is in bed, recovering in the infirmary, try to sleep in the bed next to him. The ordeal was tiring for you too, after all.
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Aviation School Isn't For Show
Defeat the Crooked Man in Scene 2 without taking any damage

Defeat the Crooked Man in Scene 2 without taking any damage. Just like in the Uncrooked Man achievement, work with the range of your knife and find a rhythm of swipe, then run, swipe, then run. It shouldn't be any tougher.
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Emily's Poem
Read the books in the hospital day-room

Scene 3, in a hospital. There will be a book singled out in what is called the day-room. Read the book for the achievement.
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Sniper

During a confrontation where you use a gun to defend Fluffy from the Crooked Man, you can't miss any shots. Every hit on the Crooked Man. My advice is just stay focused and try not to get too annoyed by Fluffy running about. It'll take a few tries, but feasible. Obviously cannot be tried at the same times as the "Oops..." achievement.
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Oops...

During a confrontation where you use a gun to defend Fluffy from the Crooked Man, shoot Fluffy. Not too hard to achieve naturally, since he is constantly in the way during that segment, but missable all the same. Obviously cannot be tried at the same time as the "Sniper" achievement.

See You Later, Duke

A completion achievement for the second run of the game.

While the rest of the achievements are more or less able to be accomplished in one play-through, a second run entirely is required for this achievement to work. When you beat the game once, you are given an area to save your data in and then move on to another run. You will know you have done this because a bright, red notification will be in the upper-righthand corner at all times.

This second run will give you further insight on the life and thoughts of the Crooked Man during Scene 5 of the game. Like "Bye-Bye Black Bird", the achievement will spawn after the credits.